反应 #674372

ord-33114cb8a6f441e78678e62c62157006

反应方程式

CCOC(=O)c1ccc(C=O)cc1C
Ethyl 4-formyl-2-methylbenzoate
Cc1cc(C=O)ccc1C(=O)O
4-formyl-2-methylbenzoic acid
O=S(=O)(O)O
H2SO4
C=Cc1ccc(C(=O)OCC)c(C)c1
title compound
收率 80.0%
C=Cc1ccc(C(=O)OCC)c(C)c1
Ethyl 2-methyl-4-vinylbenzoate
收率 80.0%

溶剂

反应条件

温度
80°CELSIUS
详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    温度The reaction mixture was cooled to 25° C.
  2. 2
    浓缩concentrated under reduced pressure
  3. 3
    workup.ADDITIONThe residue was diluted with EtOAc
  4. 4
    洗涤washed with water
  5. 5
    洗涤The combined EtOAc extracts were washed with brine
  6. 6
    干燥dried over Na2SO4
  7. 7
    浓缩concentrated under reduced pressure

实验过程

Ethyl 4-formyl-2-methylbenzoate (AI16). To a stirred solution of 4-formyl-2-methylbenzoic acid (3 g, 18.2 mmol) in EtOH (30 mL) was added conc. H2SO4 (2 mL) and the reaction mixture was heated at 80° C. for 18 h. The reaction mixture was cooled to 25° C. and concentrated under reduced pressure. The residue was diluted with EtOAc and washed with water. The combined EtOAc extracts were washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford the title compound as a solid (2.8 g, 80%): 1H NMR (400 MHz, CDCl3) δ 10.05 (s, 1H), 8.04 (m, 1H), 7.75 (m, 2H), 4.43 (m, 2H), 2.65 (s, 3H), 1.42 (m, 3H).

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US09226500B2uspto-grants-2016_01